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NARRATOR: On the 7th of September 2006, three people were gunned down on a street in the city
00:00:12
of Bridgeport in Connecticut. The youngest victim, nine-year-old Kylie Flannery,
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had been chased down by the lone gunman and executed at close range. All of this unfolded in a matter of minutes,
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so for anybody witnessing this, it must have been like watching a scene from a movie play out
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but knowing that it's all too real at the same time. The killer was 41-year-old Richard Roszkowski
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whose infatuation with Kylie's mother, Holly Flannery had come to a head in the most tragic of circumstances.
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Even though Holly Flannery was clearly in some fear of Richard Roszkowski, I don't think, for one moment,
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she could have imagined that would effectively mean the end of her life and her daughter's.
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NARRATOR: Roszkowski was eventually sentenced to death for killing Kylie and given life sentences for the murders
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of her mother Holly and tree surgeon Tommy Gaudet, a man with no connection to the Flannerys.
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EILEEN POTKAY: Roszkowski, he's absolutely evil. I hate him, and I'm glad that I never
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have to be in the same room ever again with him. NARRATOR: Richard Roszkowski had emerged as one of the world's
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most evil killers. [MUSIC PLAYING] In May 2009, 44-year-old Richard Roszkowski was sentenced to death for the murder
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of three people in a short yet bloody killing spree 2 and 1/2 years previously. His youngest victim, Kylie Flannery,
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was just nine years old. The twisted killer had become fixated with Kylie's mother, Holly.
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It was an obsession that led to tragedy, which played out just after 9:00 AM on a quiet sunny morning
00:02:24
in Connecticut. Local news reporter Daniel Tepfer was one of the first journalists at the scene.
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DANIEL TEPFER: It's a case I'll never forget. I, actually, was on my way to work that morning
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when I got a call to get over to Seaview Avenue, and I got there. The police were still there.
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They were still interviewing witnesses. And I started talking to some of the witnesses there,
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and I was just appalled at what they were telling me had occurred. And these are things that will stay with me forever.
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NARRATOR: At his trial, Roszkowski claimed to be insane and in a drug-induced haze
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during the killing spree. The prosecution team of C. Robert Satti Jr. and Margaret E. Kelley helped put him behind bars.
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I've been doing this for a long period of time, actually 40 years. What was especially difficult in this case
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was the fact that he executed Kylie in the manner in which he executed her, shooting her once until she fell
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and then walking up to her and giving her the coup de grace, killing her. MARGARET KELLEY: It opens your eyes to the fact
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that in the blink of an eye, things can change. And I remember it being a beautiful day,
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and here's a young girl going to school with her mother. Next thing you know, there are three people dead,
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and I'm sure that for the people that were in the area at the time and what they may have seen
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or heard or witnessed, it's just how things can tragically change in just a split second.
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NARRATOR: During a second trial in 2014, Roszkowski would show a remorseful side,
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but behind the facade lay a deadly killer. He had been sent to the state's maximum security
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mental hospital sometime after his arrest, and the head of the hospital who's
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dealt with the worst of the worst called the judge and said, could you please take him out here?
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We can't handle him. He's too dangerous for us. That might give you an idea of the kind of person
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that Richard Roszkowski is, cold-blooded, no moral compass, no conscience. NARRATOR: This killer story begins in January 1965.
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All we know about Richard Roszkowski's background is what he told the authorities after his arrest.
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Roszkowski was born in the US, and the information about his background is quite patchy.
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And we're quite reliant on the things that he said about it, so we did have to take it
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with a bit of a pinch of salt. But one of the things that he says is that his father
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didn't really bother with him. He felt that his father was quite distant. From what I remember, not a good student in school, got
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involved in drugs early on, was rarely in school later on, and he used to get in trouble--
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little things, thefts and vandalism and that kind of thing. NARRATOR: At a very young age, Roszkowski and his family
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visited his mother's homeland, Poland, which he says is where his troubles with substance abuse
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began. Roszkowski claims that he first tasted alcohol when he was around five or six years old.
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And then, when he was 10, he started misusing substances, like marijuana and glue sniffing,
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and that then progressed on to other things. GEOFFREY WANSELL: Glue sniffing leads to cannabis.
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Cannabis leads to cocaine. Cocaine leads to heroin. That all leads to a drug problem,
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and we're now still only a teenager. NARRATOR: Roszkowski was small in stature,
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something that led to him being picked on during his formative years. Roszkowski claims that his family moved to a new area
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during his childhood, and this area was quite deprived. It was quite poverty-stricken, and it
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was an area where there was quite a lot of criminal activity going on. And he claims that he was bullied by the local children
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in the area, and then later on, the people who had bullied him forced him to join some kind of gang.
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So again, we've got all of these external factors that are compelling me to behave in a particular way.
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NARRATOR: Life didn't get any easier for Roszkowski. He struggled with his drug addiction
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and couldn't hold down a regular job. Roszkowski lived quite a transient life as an adult.
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He flitted from job to job. If you think of the impacts on that, Roszkowski doesn't have this consistent group of people
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around him, either colleagues or neighbors, who act as a bit of an informal check on our behavior.
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So he is off the radar, in many senses of the term. NARRATOR: Roszkowski's mother had a house on Trojan Drive
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in Bridgeport, Connecticut, and her son would sporadically live with her. During this time, he got to know another resident
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on the street, Holly Flannery. ELIZABETH YARDLEY: She got to know Roszkowski's mother quite
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well and spent quite a lot of time at her house, and she gets to know Roszkowski through his mother.
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And I think because of the kind of person Holly was, I think she probably showed
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him some kindness and some empathy and some compassion. NARRATOR: Holly Flannery lived on Trojan
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Drive with her husband and her daughter Kylie. But according to witness testimony from the case,
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Holly and Roszkowski became close in the early 2000s. On the surface, Holly seemed to be
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a really wonderful person, a good mother, a great wife. She did everything that you would think is a normal mother
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and a housewife would do, but below the surface, there was something dark there.
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It was something that would cause her to be attracted to Richard Roszkowski. NARRATOR: By 2004, Roszkowski was serving three
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years in prison for burglary. Court documents show that Holly would visit and speak
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with him on the phone. Holly did correspond with Roszkowski in prison, and I think this came from a place of kindness
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and a place of concern. I think she believed he was somebody who'd had several disadvantages in life,
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and she was acting out of friendship to him. But in terms of the way he interpreted her kindness,
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he became fixated with her. He became obsessed with her, and it didn't take long before Holly started to become actually
00:09:06
quite fearful of this man. NARRATOR: In a letter Holly wrote to a friend in January 2004, she stated that she'd
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spoken to Roszkowski over the phone while he was still in prison. She said that she'd been threatened by him
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and was told she was going to go off a cliff. Chillingly, she added, if I should turn up dead,
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tell Kylie I loved her. [MUSIC PLAYING] When Roszkowski is released from prison in 2005,
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he moves in with his elderly mother, so he is in Holly's daily life. She sees him day in, day out, going about her business.
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And I think this is the point at which his fixation and obsession with her intensifies,
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and some of his behavior towards her starts to be quite concerning. It was obvious, at some point, that she realized that he was
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completely out of control, that she had no longer could control him, and he had become a threat not
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only to her, but her daughter who she worried much more about. NARRATOR: In case files, Holly's friends
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stated that she appeared more anxious and was afraid of her obsessive neighbor. At one point, Roszkowski broke into Holly's house
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and threatened her with a gun. GEOFFREY WANSELL: I doubt very much whether she encouraged it,
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but like all stalkers, they don't pay attention to reason. They act irrationally, and no one could demonstrate that more
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accurately than Roszkowski. There was one particular incident in July 2006 where Holly said that Roszkowski had pinned down and shaved
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some of her hair off. And he said to her that he wanted to basically mess up her hair, so no other man would want her.
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So at this point in time, his behavior has crossed the line to physical violence.
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He may have been following her before. He may have been spying on her, but now, he's actually
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physically harming her. So he thinks that Holly is his possession. He thinks that he owns her, and this is
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a really dangerous place to be. [MUSIC PLAYING] NARRATOR: Richard Roszkowski had grown
00:11:23
completely obsessed with his former neighbor, 39-year-old Holly Flannery. The ex prisoner and ne'er-do-well was known
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to the authorities, but there appeared to be no reason for concern. DANIEL TEPFER: He had a number of arrests for drugs or thefts.
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He was flying below the radar. He was the kind of person that you wouldn't even generally give notice to.
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He's just someone-- someone in the crowd, I guess. NARRATOR: Roszkowski's mother had moved away
00:11:56
from Trojan Drive, and the 41-year-old was now living a transient life around Bridgeport, Connecticut.
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He'd previously been staying in lodgings on nearby Seaview Avenue. MARGARET KELLEY: He was living in this rooming house
00:12:12
with some other individuals. There was some testimony during the trials from one of the individuals that there was a drug use going on.
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NARRATOR: Not all of the tenants at the house on Seaview Avenue were criminals. Just before Roszkowski had been asked to leave by the landlord,
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he'd crossed paths with a 38-year-old tree surgeon named Tommy Gaudet. He'd been living in this rooming house on Seaview Avenue
00:12:38
with other people who had been working at the landscaping company. He had been separated from his family
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and was hoping to turn his life around and get back to them. ELIZABETH YARDLEY: So their paths had crossed,
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and they knew of each other. But I think in the brief time that they have instructed,
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Tommy had clocked that Roszkowski was not a nice individual. He had noticed that he was unpredictable,
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and he was the kind of person to give a wide berth to. NARRATOR: Tommy Gaudet had two children
00:13:07
who meant the world to him, which his sister Eileen Potkay testifies to. EILEEN POTKAY: Oh, my God.
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You know what? I'm actually getting goose bumps just thinking about it. When my niece was born, it was probably
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one of the most wonderful days of his life to have a baby girl, and he was hands on.
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He changed her diaper. He fed her. He burped her. He went shopping for her clothes.
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When he became a father, he was an amazing dad to Natasha. And it was many years later that he
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had a son, so Natasha was alone for many years with Mommy and Daddy. But my brother was a very hands on dad, and he adored her.
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NARRATOR: In September 2006, Thomas Jr. was 10, and Natasha was 14. NATASHA GAUDET: I remember going in his cherry picker.
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He was a tree man. And he worked for a tree company, and he used to have this big truck with--
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like the firemen have, like the big bucket on top. And I remember going in there, and, you know, feeling
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like I was on top of the world. THJOMAS GAUDET JR.: My dad was a great dad. He made sure that we were always having
00:14:15
the best time as possible. I think, him growing up, he didn't have the best father
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figure, so he definitely wanted to make sure that his children had, you know, so
00:14:24
much better than what he had. The last time I spoke to my dad, I was in the driveway hanging out,
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and he stopped by and said, hello. And that was the last time I saw him. NARRATOR: Tommy Gaudet got up for work
00:14:38
on the 7th of September 2006, but he never made it that far. At some point during the morning,
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Tommy and Richard Roszkowski had a heated exchange over the phone. Roszkowski phones Tommy and basically,
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accuses him of having a relationship with Holly. And Tommy just thinks this guy has lost it.
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He remembers Roszkowski his behavior and just thought, oh, this is just him kicking off again.
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NARRATOR: Three miles across town on Trojan Drive, Holly Flannery was getting her nine-year-old daughter
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Kylie ready for the first day at her new school. DANIEL TEPFER: According to testimony at trial,
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it had started out as a very normal morning. Holly had gotten Kylie up to get ready to go
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to Thomas Hooker School. NARRATOR: But the nine-year-old would never make it to school.
00:15:32
Holly and Kylie's 41-year-old former neighbor had finally snapped. After months of intimidation, Richard Roszkowski
00:15:41
was about to put his deadly threats into practice. Roszkowski went into a rage, a rage
00:15:50
that most people certainly wouldn't be able to understand, and I don't understand.
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But he somehow imagined that Holly was cheating on him. She had broken off their relationship,
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and he was determined to confront the man he believes she was cheating with. NARRATOR: Somewhere in Roszkowski addled mind,
00:16:12
he believed that Holly and Tommy Gaudet, who were strangers to one another, were in a relationship.
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It has never been established under what circumstances the trio traveled to Seaview Avenue,
00:16:25
although Holly's car was eventually recovered from the scene. But just after 9:00 AM, Roszkowski,
00:16:33
Holly Flannery, and her daughter Kylie arrived at the boarding house. Now, in terms of Roszkowski thinking,
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he was like a missile at this point. Here is a man who is very fixed and very rigid in his thinking.
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He's decided that he's going to kill Tommy on this day, and that is exactly what he follows through.
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DANIEL TEPFER: He was just standing outside the house. He was just simply just standing there, outside this rooming
00:17:00
house when Roszkowski decided, for whatever reason was going through his head, that Gaudet must
00:17:07
be the man that she was cheating with even though they had never even met. NARRATOR: One thing we can be sure of is, at some point,
00:17:15
Richard Roszkowski pulled out a gun. Gaudet yelled at him. Like, what is going on here?
00:17:21
Hey, what's going on? And was immediately shot in the head. But once Gaudet is dead, it's as if the lock is taken off
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Roszkowski's self-control, and he grabs Holly Flannery in a headlock on the street, in front of her daughter Kylie,
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puts his arm around his head, and Holly's shouting, screaming. She started screaming, not in front of my daughter,
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not in front of my daughter. He then shot her once in the head. She falls to the ground.
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And then, poor Kylie just doesn't know what on Earth is going on, and trying to make sense of it,
00:18:01
she runs for her life. He then runs after her, catches up with her, shoots her in the back, causing her to fall down
00:18:09
on the sidewalk on her back. She's face up, screaming, crying. He then walks and stands right over her and fires
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into her face. NARRATOR: In less than three minutes, Tommy Gaudet and Holly Flannery had been shot dead,
00:18:28
and Kylie Flannery was fighting for her life. The nine-year-old who'd meant to be starting a new school
00:18:35
that morning had been chased along a suburban street and shot three times at close range by Richard Roszkowski.
00:18:45
So Kylie is a 9-year-old girl. She's just seen her mother shot dead in front of her.
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She's seen her mother's killer kill somebody else. So I think it's sheer terror in terms of what's
00:18:58
going through her mind. It's very difficult to process that amount of trauma
00:19:02
and work out what on Earth is going on. So her immediate reaction is to just get away,
00:19:08
get out of there. The thought of that little girl, Kylie, running down the street, her flip-flops flying off as she
00:19:18
ran, scared to death, and then to be shot and laying on the sidewalk face up when Roszkowski stood over her
00:19:27
and fired the final shots, I can't even imagine it had happened. NARRATOR: Paramedics rushed Kylie to a hospital,
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but her injuries were too severe. Despite efforts by doctors to resuscitate the nine-year-old schoolgirl, they couldn't save her life.
00:19:46
GEOFFREY WANSELL: There could be no excuse for this. To take the life of a 9-year-old child lying at your feet whom
00:19:51
you've shot in the back and you decide to execute her effectively by shooting it twice in the head, that
00:19:58
is profoundly, profoundly wicked act, which I think does justify the use of the word "evil."
00:20:07
NARRATOR: Three people were now dead at the hands of Richard Roszkowski, and the drug-addicted killer
00:20:13
was on the run. His obsession with his 39-year-old former neighbor had led to tragedy.
00:20:21
Let there be no doubt that Roszkowski was erratic. Let there be no doubt that he'd always
00:20:29
lived on the edge of society and that he consoled himself with drugs and crime. The tragedy of this entire case is his fixation
00:20:41
on Holly Flannery, because without that, these killings would not have happened.
00:20:45
He decides on a course of action, and he literally just goes and carries it out.
00:20:50
So any time that morning on the way over to the boarding house, in between killing Tommy and Holly,
00:20:56
in between killing Holly and Kylie, he could have decided to stop. He could have decided not to kill anybody else,
00:21:03
but that was never going to happen, because he had a plan and he was going to follow it through.
00:21:09
NARRATOR: Detectives arrived at a scene of carnage. A beautiful sunny morning had been darkened by a killer
00:21:17
who remained unaccounted for. Police had no idea who it was and no idea if he was going to strike again.
00:21:27
After chasing nine-year-old Kylie down the street and shooting her at point-blank range,
00:21:32
Roszkowski had taken flight. GEOFFREY WANSELL: He doesn't run down the street.
00:21:38
He runs through gardens, jumping over fences in an effort to escape. Because it is 9 o'clock in the morning, in broad daylight,
00:21:47
plenty of people out, and he's committed three ruthless killings in a matter
00:21:52
of moments in plain sight. This is not a man killing in private. This is a man killing in full public view.
00:22:02
Roszkowski flees on foot, taking clothing from clothing lines on the way so that he
00:22:07
can change his clothes and make it look like he's somebody else. So he's got the presence of mind to do that.
00:22:14
He also pulls over a motorist and offers them some gas money to give him a lift to his mother's house.
00:22:22
NARRATOR: While Roszkowski made his escape in an unknowing stranger's vehicle,
00:22:26
detectives were already onto him. The roommate of Tom Gaudet, who came out shortly
00:22:32
after the shooting, gave the name of a Richard Roszkowski, and he gave the police the location of his mother's
00:22:38
residence in Trum. NARRATOR: Roszkowski would not remain a fugitive for very long.
00:22:44
C. ROBERT SATTI: He was arrested in the town of Trumbull with the assistance of Trumbull police officials
00:22:50
who had set up at his mother's residence, what-- just happened to be at the dead end of the street,
00:22:57
so they were able to set up a perimeter. And Mr. Roszkowski just appeared to have no affect and emotion
00:23:03
at that particular time. NARRATOR: Across town, stunned journalists had started arriving at the bloodied sidewalks
00:23:11
of Seaview Avenue. DANIEL TEPFER: When I arrived at the scene, it appeared there was pandemonium.
00:23:17
People were all over the place. The police had blocked off most of the streets in the neighborhood.
00:23:23
They were out questioning people. I came upon a man sitting in a pickup truck. He was a landscaper, and he was just
00:23:30
sitting there, slumped over the steering wheel of his truck, obviously in distress.
00:23:38
So I went over to ask him, you know, what's going on? Well, as it turned out, he had been driving down
00:23:43
the street on Seaview and had seen, had seen the little girl getting shot, and it was just so upsetting to him that he had to pull over.
00:23:51
He couldn't drive anymore. I, then, went and talked to some other witnesses,
00:23:56
all had similar accounts and all who were visibly distressed. It's just something that it's very hard to comprehend.
00:24:05
NARRATOR: The junction of Seaview Avenue and Boston Avenue is a busy intersection during rush hour,
00:24:12
and many passing motorists had witnessed the very public murders. DANIEL TEPFER: One woman recalled
00:24:19
hearing Holly Flannery scream, not in front of my daughter, you know? She remembers hearing that but didn't really see that much.
00:24:27
I mean, it was just-- everybody had little bits and pieces of things that they had seen or they had heard,
00:24:33
and you just had to kind of try to put together like a puzzle. NARRATOR: Many of the witnesses described
00:24:39
how calm Roszkowski appeared to be during the shooting. This wasn't somebody who was losing it, who was going mad,
00:24:47
who was on a rampage. And it's very tempting to interpret his behavior in this way because of how close together
00:24:54
these murders were, but I think he knew exactly what he was doing. And if you listen to the witnesses describe it,
00:25:01
they talk about him walking and seemingly being unaffected by what he'd just done.
00:25:07
NARRATOR: The murder of three people, one of them a child, had completely shaken the community,
00:25:14
especially the people who turned up to help. C. ROBERT SATTI: It was testified too
00:25:19
that the ambulance driver and the medic was impacted very deeply because he had a child,
00:25:25
and it may well have been a daughter about the same age of Kylie. I do know, in talking to the law enforcement
00:25:32
officials that were there, it impacted all of them deeply. ELIZABETH YARDLEY: I think the impact on the local community
00:25:38
would have been immense. This is not the kind of place where multiple murder happens.
00:25:43
People would have just been going about their daily business, going to buy a paper,
00:25:48
taking the kids to school, getting their morning coffee, and in front of them, the scene of carnage emerges.
00:25:54
So I think it has left a scar on the community in terms of the feeling of safety and security in your own street,
00:26:03
in your own neighborhood, and the fact that people like this, they walk among us.
00:26:08
They often don't look like monsters, so it does make us question everybody around us.
00:26:13
NARRATOR: As investigators at the scene began to identify the victims, they reached out
00:26:19
to the family of Tommy Gaudet. EILEEN POTKAY: I got the phone call. And I was driving in the car, and I pulled over.
00:26:25
And they're telling me that my brother has been killed and that there was a woman and a child with it also,
00:26:31
and I just couldn't wrap my head around the fact that, how is this all connected?
00:26:36
And she just kept repeating it to me, that, you know, we're trying to put the pieces of this together
00:26:40
and that my brother had been leaving for work and was gunned down when he exited his door.
00:26:44
That's how I found out. I remember waking up to my mom on the phone, talking really loud saying, you know,
00:26:52
what are you talking about? This can't be happening. Let me walk outside. Thomas is sleeping, talking about me, and I was like,
00:26:59
what's going on? So me, as a curious 10-year-old, I decided to turn on the news,
00:27:03
and I saw, you know, the helicopter scene of the scene, you know? All they said was a, you know, three people have been killed,
00:27:14
and the aerial view of the house was where my dad lived. And I had recognized it because I had been there,
00:27:19
you know, just a few weeks prior, so I stumbled out of bed, went outside, found my mom and my sister in the driveway crying.
00:27:27
And I was like, what's going on? I know that my dad walked out of his house and got ambushed and shot in the head, and I don't know why.
00:27:40
That's all I know. [MUSIC PLAYING] NARRATOR: It appeared that Richard Roszkowski
00:27:50
had killed Tommy Gaudet because of misplaced jealousy and paranoia. There's a lot of different stories and theories
00:27:59
about what happened. I remember hearing, like, a lot of different lines. Like, it was a love triangle, a crime
00:28:05
of passion, just a bunch of crap, a bunch of mishmosh stories with no facts or evidence behind them but, I guess for the views--
00:28:14
ELIZABETH YARDLEY: Before the day of the murders, Holly and Tommy had never met one another.
00:28:19
They were not known to each other in any capacity whatsoever, and the only place that they had come together
00:28:24
was in Roszkowski's imagination. He had become so fixated on Holly, so obsessed with her
00:28:31
that he would sit and ruminate and think and make up scenarios in his head that he would
00:28:38
convince himself were real. [MUSIC PLAYING] NARRATOR: When Roszkowski's name was released to the public,
00:29:20
Thomas Jr., who was just 10 at the time, recognized his father's killer. When they put his mugshot on the news,
00:29:29
I immediately had a flashback to, you know, just a couple of months prior for my birthday
00:29:35
when my dad was visiting and came to give me a birthday card, and Richard actually drove him,
00:29:40
because they were roommates. So I immediately was like, oh, my gosh, mom. That's the guy who is dad's roommate,
00:29:47
and he gave me 20 bucks for my birthday. NARRATOR: Days after the shootings, the Gaudet family visited the crime scene on Seaview Avenue.
00:29:58
There were a lot of police officers, of course, a lot of bystanders, a lot of balloons, a lot of Teddy bears.
00:30:04
I didn't know if those were for Holly and my dad or if they were for Holly's daughter.
00:30:10
NATASHA GAUDET: He killed a 9-year-old little girl. She was a baby. My son is 10.
00:30:15
She was nine years old. I mean, not that it justifies my father or that-- Holly's death or anything like that or it
00:30:22
minimizes it, but to kill, to empty the clip in a little girl while she's running from you, that's, like, beyond evil.
00:30:30
I know this for 100% certain that if my brother had had the opportunity that day to protect that little girl
00:30:37
and save her life, he would have. He loved children. [MUSIC PLAYING] NARRATOR: Roszkowski told detectives
00:30:45
that he'd been gorging himself on drugs in the days and hours leading up to the murders, and he continued to claim to have
00:30:53
no memory of the incident. To my understanding, from what I hear and from what I know,
00:31:00
he was doing crack and heroin, and he was on a long drug binge that had been going
00:31:06
on for days, a lot of drugs. We're talking Xanax, marijuana, alcohol, heroin, crack.
00:31:12
We're talking a lot of drugs in his system. NARRATOR: As well as his out of control drug addiction,
00:31:18
detectives discovered Roszkowski's motive behind the murders. During the police investigation,
00:31:25
they learned of Roszkowski's rather transient, chaotic lifestyle, and they learned of his previous stints
00:31:33
in prison and his drug use. They also come to learn about Holly's experience,
00:31:39
being victimized by Roszkowski, so the picture starts to emerge of a man who feels entitled to behave
00:31:46
in whatever way he wants. He's very fixated. He's very rigid in his thinking, and he is self-obsessed.
00:31:53
He is me, myself, and I. He has very little concern for other people. [MUSIC PLAYING]
00:32:02
NARRATOR: Just under three years later in May 2009, 44-year-old Richard Roszkowski went
00:32:08
on trial at the superior court in Bridgeport, Connecticut. He was charged with murdering Holly Flannery,
00:32:16
her nine-year-old daughter Kylie, and tree surgeon Tommy Gaudet. Tommy's family were in attendance
00:32:23
throughout the hearing. I just remember seeing him and, you know, asking my mom like, can he come out from behind there?
00:32:33
Can, you know, he get us? And, you know, of course, that's a fear. This person just killed your dad.
00:32:39
Can they come and kill you next? There were times where he was literally feet away from me,
00:32:45
and that, you know-- that thought comes over you. Like, wow. I can-- maybe I can get him, and it's almost
00:32:52
like you want to attack him. And it brings up something inside of you because you're-- you're just thinking he's so close to you,
00:32:58
but it's uncomfortable to be that close to a killer, a killer that could take two adults and a child's life
00:33:03
within three minutes. Three minutes, they're all dead. NARRATOR: Roszkowski claimed to have no recollection
00:33:10
of the murders and therefore, was not in control of his actions. The defense tries to claim that Roszkowski is insane,
00:33:19
and by implication, he's not responsible for his actions. And Roszkowski does play up to this.
00:33:27
So he exhibits some signs of shaking and stuttering in his speech and trying to appear
00:33:34
in a very stereotypical way to be somebody who is insane. NARRATOR: As well as a claim of insanity,
00:33:41
Roszkowski stated that he'd been on a drug binge that lasted for days in the lead up to the killings.
00:33:49
Supervisory assistant state's attorney C. Robert Satti Jr. led the prosecution.
00:33:56
C. ROBERT SATTI: There was a substantial defense that was put on. It took two different forms.
00:34:00
One was a claim of intoxication, and the intoxication went to the fact that Mr. Roszkowski, if the jury
00:34:06
determined that he was intoxicated, we had to disprove that and show that his intent was not going
00:34:13
to be mitigated or actually, if he was intoxicated, was an absolute defense of the crime.
00:34:17
So I do recall that there was an intoxication claim being made, and they put a lot of witnesses on concerning that.
00:34:24
There was also a challenge as to the mental status of Mr. Roszkowski. ELIZABETH YARDLEY: He was basically trying to say,
00:34:31
this is not my fault, you know? Poor me, look at me. I'm suffering from a terrible condition.
00:34:36
But it was very clear in terms of his behavior around the offenses that he did know what he was doing.
00:34:43
He had a presence of mind. He was constantly making decisions and making choices.
00:34:48
Had he been legally insane, had he been suffering psychosis or something like that, driving him to behave
00:34:55
in a particular way, he would not have been anywhere near as organized as he was.
00:35:01
NARRATOR: Many of the witness statements from the day painted a very different picture, that Roszkowski was calm
00:35:08
and in control of his actions. NATASHA GAUDET: Where he killed them, there was a light,
00:35:13
and there was a row of cars. So there were people who literally looked in the mirror
00:35:18
and saw these people get shot and killed and murdered through their rear view, that were testifying that day.
00:35:24
DANIEL TEPFER: It was a tough testimony. No question about it. It was tough for everyone in the courtroom to hear.
00:35:30
I'm sure was tough for many of the witnesses to testify about it. Some of them cried.
00:35:37
Looked over at the jury, some of them were crying. It was obviously something that they had never
00:35:42
heard before, maybe never even imagined before, but now, on top of it, they would have to hear to decide
00:35:48
someone's guilt or innocence. NARRATOR: Ultimately, Roszkowski's plea of insanity
00:35:54
fell on deaf ears. I think the jury needed to understand that Mr. Roszkowski was responsible for his actions and knew
00:36:03
what he was doing when those three people were executed. We had argued that it was an extreme, cruel activity that
00:36:12
occurred in the killing of her that I suggest led to the finding of the jury that Mr. Roszkowski
00:36:18
deserved the death penalty. The verdict was guilty on the capital felony, and he was subsequently sentenced to death.
00:36:27
NARRATOR: But, in an agonizing twist for the victims' families, a legal technicality meant
00:36:33
the judge was forced to overturn the jury's decision. Roszkowski's conviction was upheld,
00:36:40
but a second sentencing trial would have to take place in the future. In December 2011, Roszkowski was interviewed in prison by
00:36:51
psychiatrist Dr. Howard Zonana. He still claimed to have no memory of the events.
00:37:13
NARRATOR: Roszkowski did, however, allude to a reason behind the killing spree. He claimed to have discovered a letter in his mother's home
00:37:22
on the morning of the 7th of September 2006. INTERVIEWER: Right. NARRATOR: No letter has ever been found by police
00:38:35
investigating the murders, and no link between Tommy Gaudet and Holly Flannery has ever been established.
00:38:43
Richard Roszkowski's resentencing trial took place in 2014, and this time, he was given the opportunity to speak
00:38:52
to the families of his victims. Like I said, is I'm truly, deeply remorseful
00:39:00
for what happened, and I'm truly sorry for the pain that I have caused to you and to all the family members.
00:39:09
I am truly, truly sorry for your pain. He says, I feel sorry. I feel remorse. And for me, that's a bit of a red flag,
00:39:18
because just parroting the words sorry and remorse don't actually mean that you are sorry or remorseful.
00:39:25
It's more convincing for me when offenders are talking about how they feel, what kind of physical emotions
00:39:31
they're feeling. I would like to believe that he was sincere, but I don't think he was.
00:39:37
I think he was going through the motions of saying it. I don't think it was accurate.
00:39:41
I don't think it was believable. NARRATOR: In May 2014, the results of the second trial
00:39:48
was the same as the first. Richard Roszkowski was sentenced to death, but because Connecticut had abolished the death penalty
00:39:55
in 2012, his sentence was eventually changed to life without the possibility of release
00:40:02
at a third trial in 2018. I was just relieved and I'm glad that he'll never
00:40:08
ever see the light of day, and he can't harm anybody else ever. He's damaged and changed a lot of lives with what he did.
00:40:16
And that other family has to live without their granddaughter, and they lost their daughter.
00:40:20
We have to live without my brother. My niece and nephew lost their dad, but for that other family, that mother
00:40:26
lost her daughter and her granddaughter, you know? It's horrible, absolutely horrible.
00:40:33
NARRATOR: We may never know the real reason why Richard Roszkowski decided to kill three people in September 2006,
00:40:42
but there seems to be no doubt that it was driven by his obsession with Holly Flannery.
00:40:50
DANIEL TEPFER: There's always been questions about what the relationship was.
00:40:54
There'll always be questions. I mean, people will never really understand what it was that attracted her to Richard Roszkowski.
00:41:03
I mean, that's one of those things that will never be answered. I don't think we will ever know the true nature
00:41:09
of the relationship between Holly and Roszkowski, because Holly has been silenced.
00:41:14
She's never going to be able to tell her side of the story, and anything that Roszkowski says,
00:41:19
we really have to take with a pinch of salt. And very often in these cases, we look at the victim's behavior.
00:41:25
What did they do to provoke their offender? Did they do anything to encourage him?
00:41:30
And I'd say, no. The only person responsible for these murders is Roszkowski,
00:41:35
and that's what we need to remember. NARRATOR: Roszkowski's infatuation with Holly led not only to her death and the death
00:41:43
of her daughter, but also a man who'd never clapped eyes on either of them until just seconds
00:41:50
before he was executed right outside his home on Seaview Avenue. [MUSIC PLAYING]
00:41:58
EILEEN POTKAY: Tommy should be remembered for, number one, being a hard worker, number two, being the best dad ever.
00:42:05
He adored his children. And number three, he was the best uncle to all the nieces and nephews he had.
00:42:11
They all adored him. And he's loved, and he's missed. WOMAN (ON VIDEO): Who's that Ray Ray?
00:42:16
What's his name? Uncle Tommy. His grandkids, my kids ask about him all the time,
00:42:25
and they always say they would have loved to meet him and sad that they will never get to meet up.
00:42:32
At least, I had him for a little bit. I had him for a little while. [MUSIC PLAYING]
00:42:40
NARRATOR: Richard Roszkowski will never be able to ruin any other lives. The dangerous killer will remain behind bars
00:42:47
for the rest of his days. My experience, listening and seeing Roszkowski, he's one person that can never be rehabilitated.
00:42:56
He is just one of those rare individuals that's just so bad that he should never be able to walk where
00:43:03
the community is ever again. NARRATOR: Roszkowski was completely fixated on Holly Flannery, and whatever their relationship,
00:43:14
nothing could justify his actions. To kill the woman he obsessed over, her 9-year-old daughter, and an uninvolved father of two
00:43:24
in a bloody public execution undoubtedly makes Richard Roszkowski one of the world's most evil killers.
00:43:32
[MUSIC PLAYING]